Upping the Ante Ch. 03-04

[This story is a continuation of the latest in the series of stories about Margaret, the shy widow next door, and her evolving relationship with her new Master Will. It has many aspects and could have also been listed under the Mature, Anal, Exhibitionism, bisexual, trans, and BDSM categories, among others. It has considerable references to bodily functions, so if that is not your cup of tea, please read no further. All characters in this story are well over 18 years old. You will understand these chapters much better if you read chs. 1 & 2 first.]

Chapter 3

By now, afternoon was gliding into early evening, and with their sexual hunger temporarily sated, the two depraved couples were beginning to feel hunger pangs of a different sort. Will had foreseen this occurring, and before Constance and Neville had even arrived, he had phoned in a reservation for four at eight o'clock at La Traviata, an Italian bistro within walking distance of their apartment complex. Their menu was delicious without being pretentious, and their service was extremely accommodating.

The opera crowd was their core clientele, which meant they had a seasoned tolerance for both flamboyance and those wishing discretion. It was the perfect spot to bring Constance and Neville for an exquisite repast.

In anticipation of dinner, the two couples repaired to their respective apartments to wash up and dress for an evening out. Margaret raided her wardrobe for a fresh ensemble which she brought back to Will's apartment. Connie and Nellie put their own luggage and clothes in order and similarly dressed themselves for an elegant time.

With Nellie's next iteration of punishment on temporary hold, he dolled himself up into an angelic vision of beauty, all feminine frills, lingerie, and a most lovely green evening gown clinging to his slender form. His light brown hair flowed gently past his shoulders, nicely framing his face.

Reluctant to subject herself to another wrapping so soon, Connie concocted a confection of gauzy swathes, scarves, and swirls around her swinging form which defied anyone's ability to discern what exactly was in play.

As they entered the restaurant, they were smoothly guided to a roomy three-sided booth in the far corner of the back room, a candle-lit cove, where prying eyes would be defeated by shadows and curtains.

Connie situated herself on the center cushion of the U-shaped booth, with Margaret on her right flank and Will to her left. With a subtle gesture, she directed Nellie to slide beneath the white cloth-covered table and take his place on all fours, lost in the darkness, his loveliness hidden from view. This was an even more wrenching punishment than his earlier anal reaming by his precious Mommy. Mommy could be so cruel sometimes. But he loved her all the same.

The dinner proceeded in its multiple courses, all brought to their booth by smartly dressed waiters who nary raised an eyebrow when bringing servings for four, with only three guests in sight. When they turned and left, Connie neatly scraped Nellie's course into the stainless steel doggie bowl she had brought in her elegant shoulder bag, and handed it to Nellie beneath the table. He gratefully plunged his face into the delicious fare, making rude gobbling and chewing sounds that were masked by the subtle piped-in arias and choruses shared through the bistro's sound system.

Having been tipped off to eschew underpants, Margaret and Will were treated to Nellie under the table delicately licking their privates while the diners enjoyed a refreshing dessert of two scoops of peach gelato. Being all rather played out, cumming was not the goal; just a little aperitif of naughty stimulation to bring the evening to a piquant close. Afterwards, Nellie crawled out from beneath the table, looking a disheveled mess, and quickly headed off to the nearby ladies room, to put himself back together.

To his chagrin, there were two other women in the room powdering their noses in front of the mirror. They did their best to pay no attention to Nellie's messy face which was covered with a slimy mix of marinara sauce, gelato, and cunt juice, but couldn't resist sharing a subtle snooty double take.

Nellie practically dove into an available stall, hoisted his splattered and soiled gown, and tinkled noisily while wiping his face with toilet tissue. It was so embarrassing, yet oh so naughty and arousing. He had to slap and flick his little penis to make its swelling go down so that he could finish his business. Once the ladies left, he quickly emerged and gave his face a good scrub, trying the best he could to bring it back to a semblance of neat order.

As the two couples made their way out of the bistro, Will slid the Maitre'D an extra tip in gratitude for their special accommodation. La Traviata was a class act and a national treasure. Will made sure that everyone appreciated their time there.

* * *

Back in Margaret's apartment, Will and Constance agreed that such a full day made it soon time to turn in. Nellie went off to take a much needed shower, while Margaret traipsed down to Will's apartment, her borrowed key in hand, and let herself in, soon followed by her own shower and donning of her favorite sheer nightie. She crawled into Will's roomy bed, awaiting his return and a nice cuddle.

Conferring over a nightcap of warming cognac, the two dominants loosely planned out the day before them. Connie conceded Saturday morning and early afternoon to Will's choice for play scenes, including a punishment for Nellie. She was pleased with how he proposed to direct the task, and truth to tell, she wished a little break from her vigilance in monitoring her husband's misbehavior. Neville was a good slave, on the whole, but his slip-ups had been increasing and she couldn't tell whether he was secretly positioning himself for more punishments, or simply falling down on the job.

After Will departed back to his apartment next door, silently entering through the door that Margaret had left unlocked for him, he washed up and joined his adorable sub in bed.

Meanwhile, Connie washed up and entered her bedroom, noting that Neville had dutifully curled up in his dog bed on the floor, shivering and trying to make himself comfortable. Connie felt a pang of pity and dug out his stuffed hedgehog, "Heathcote," from their baggage, placing it beside him in his bed, and then gently spread his doggie blanket over him. Nellie sighed contentedly. Lord knows what the next day would bring, but he was all tucked in and cozy for tonight.

Back in his bedroom, Will wrapped his arms around sweet Margaret in bed, and gathered her to him, kissing her eyes and ears, forehead and cheeks. He had plans for her tomorrow that he hoped might address her deeper cravings for submission and debasement. It was just a hunch, but he suspected her sharing Nellie's punishment might push her close to her edge.

Chapter 4

Saturday morning, the two couples fixed their own breakfasts and prepared themselves for round two of their special play weekend. As Will and Constance had agreed the night before, their two subs would be dressed identically in black latex hoods, black half-girdles, and four-inch black heels. The hoods had holes toward the back on top, allowing for the wearers' hair to be pulled out in pony-tails, while there were large oval cut-aways in front, exposing their faces from their eyebrows to mid-chin. The effect was just bizarre enough to create an exotic effect, but allow for normal breathing.

At nine o'clock sharp, Will phoned over to Constance that they were about to arrive, and then had Margaret in her hood and half-girdle precede him down the hall to her own apartment door. This immediately put Margaret into a mortified state should anyone on their floor spy them. She thought she saw someone a couple of apartments down peek out at them, but swiftly pull their head back in and shut their door. This possibility of exposure flustered her mightily, and her breathing became ragged. But still she persisted.

She knocked and Nellie promptly let them in, attired identically to Margaret. Connie herself was clad only in a black leather eye-mask of a Masquerade sort and black stacked heels, her humongous titties and swollen clitoris swinging as she walked up sensually to greet them, her large bottom grinding and swaying behind her. She and Nellie both bowed respectfully to their hosts and then stepped back, waiting for Will to start the proceedings.

Will wore a simple black eye-mask like Connie's, though he forewent the heels as not quite his style. In deference to some pedi-adornment, however, he had allowed Margaret to paint his somewhat disreputable toenails with black nail polish. Under the circumstances, this was sufficiently bizarre. Like Margaret, he had his generous body hair on full display, in contrast to the plucked and shaven skin of their guests. Will spoke calmly, addressing Nellie first.

"Nellie, Constance has given me the honor of presiding over your punishment for not one but two ejaculations yesterday without her permission. I doubt that this punishment will cure you of your bad habits, as you seem to be quite a randy fellow."

He paused for a moment, to savor Nellie's deep humiliation, his flushed cheeks displayed through the oval cut-away in the front of his black latex hood.

"Indeed, with this punishment, I hope to make it so intense that you will never forget it, and that it will remind you forever after that disobedience comes with a very painful penalty."

Nellie looked both mortified and nearly scared out of his wits. He had never played with Will before this weekend, and had no real sense of what Will might be capable of. He tried desperately to maintain his composure, but he began to tremble and sniffle as, unbidden, his little prick stiffened and twitched. Damn! The little organ had a mind of its own, betraying him time after time. He tried to just descend into his Sub Zone and let it all wash over him.

"Now Nellie, perhaps you may be pleased to hear that Margaret has agreed to undergo your punishment with you. As I think you know, she is rather fond of you -- you two have a long history of sharing your submissions together -- so everything you experience, she will experience with you. Your pain will be her pain. Your humiliation and shame will also be hers. I hope you appreciate her gift to you."

Nellie looked over to Margaret and gave her such an intense look of sheer gratitude and empathy that he almost made Margaret tear up and cry. Will was, in his calm and quiet way, stirring them up into an intensely submissive space that the two subs held onto for dear life.

"Alright, then. Would you both step into the center of the mat here and press right up against each other? Don't hold back, please. Mash yourselves together. Yes, perfect. Now, bring your lips together and open your mouths for a nice deep kiss. That's it. Now, don't move."

Will glanced over to Connie who handed him a long black velcro strap. He wrapped it around their hooded heads in a kind of figure-eight, forging a single unit of two black latex-covered heads locked in a French kiss from which they could not extricate themselves. They could breathe through their noses, and feel their tongues wrestle with each other, but it was an intimacy fraught with danger. The proximity of tender tongue flesh and teeth made them hyper-aware of not inadvertently biting or injuring each other.

Yet, they couldn't resist sucking each others' tongues and savoring their enforced dilemma, as if they were college kids petting in the back seat of a car, in some twisted fraternity-sorority initiation rite. They both shared the sense that they were being granted a brief moment of tender joy together before the hammer dropped.

Will had the two subs embrace each other, with Margaret's arms wrapped around Nellie's neck and Nellie's arms meeting at Margaret's shoulder blades. Connie snapped padded velcro cuffs on their wrists and linked them together. She then knelt, at Will's gesture, and snapped cuffs onto their ankles, linking Margaret's left ankle to Nellie's facing right ankle, and vice-versa. They could move of a sort, but it had to be in close coordination.

Finally, Will squatted and directed Nellie's stiffened little prick up into Margaret's pubic nest, carefully positioning it as a rude intruder into her hairy quim. He had no confidence that copulation might happen, but he wished to leave the possibility open. This was to be a very intimate punishment.

* * *

Will was not a fan of harsh discipline. He preferred hand spankings and paddling over canings. But in this circumstance, he thought a nice supple leather strap might fit the bill. He handed one to Connie and took up the other for himself. Time to tenderize the meat.

"Now, no screaming you two. Just kiss the pain away. The best is yet to come!"

In sync, Will and Connie began to strap their subs' lower backs, buttocks, and upper thighs lightly, getting them warmed up. Then they turned up the heat with stinging lacerations. This was the harshest that Will had ever subjected any sub to undergo. But, it was hardly the harshest that Nellie or Margaret had experienced. Indeed, they savored the strong discipline, emitting little muffled cries and moans, but surrendering to the fierce repeated blows.

The pain was almost overwhelming and the strapping seemed to go on rhythmically for an eternity, but with every blow their endorphins grew, and Margaret and Nellie soon found themselves clutching each other tightly in a profoundly intimate martyrdom. Their hardened nipples rawly rubbed against each other, a jolt of electric heat radiated through their nerves, and they melted together into what felt like a single nervous system of throbbing pain and exquisite pleasure. The boundaries between their bodies dissolved and they became a single writhing and sweating animal covered with bright red strap marks, emitting little muffled groans and cries, while their identities merged into meat space.

Then the strapping ceased and the submissive pair staggered awkwardly, trying to keep their balance with their ankles cuffed together with toes pointing in opposite directions. In their altered state, they had lost track of who they were and where they were as well. It was an oddly freeing feeling, as if they had shed the burden of identities and just "were".

But all good things must come to an end, and it was now time for Will and Connie to proceed to the final stage. As with yesterday, Nellie would have his little arse reamed, but by Will this time, while Connie would take care of Margaret's bum with her outsized clitoris. Penetrating another man's rectum was a new wrinkle for Will, one he felt somewhat ambivalent about, but Nellie, as he saw him was barely a man at all, more like an ambisexual nymph. And an oddly fetching one at that. He thought that Nellie's punishment was a good opportunity to stretch his own horizons.

Connie reached for a tube of lube and liberally spread it over Will's grizzled member and then coated her own stiffened organ with the slippery goo.

They positioned themselves behind their helpless subs and placed their respective meat-sticks into contact with the sphincters before them. This was, as before, the apex of Nellie's punishment, as his tiny anus could scarcely accommodate a full-sized cock without sharp splitting pain, unless he fully relaxed into the invasion of his rectum and let the endorphins do their work.

Margaret was wired a little differently. With years of training by her husband Paul, she had come to crave anal sex, almost to the point that she relished it more than vaginal sex. She commonly required corn-holing twice a week to maintain her mental equilibrium -- and this was in addition to almost daily bondage periods, gaggings, and spankings. Will was glad he was retired, because domming Margaret was akin to a full-time job. If he needed a day's break, to get some writing done or just to cool his jets, he knew she would resourcefully resort to self-bondage using timer cuffs and spreader bars or other of her toys.

While sodomizing Nellie might serve as a harsh punishment for the Little Man, Margaret looked forward to Connie fucking her arse with her clit as a special treat. Connie had a nasty streak that could manifest itself in unexpected ways, and Margaret loved the aura of danger that Connie exuded when she played with her. Master Will was a bit of a teddy bear as Doms go, always looking after her and making sure she felt loved. She treasured him for that.

But Mistress Constance knew just how much sweet little Margaret craved utter debasement when given half an opportunity. Margaret was sure that Connie would really work her over before the weekend was through, and the thought made her labia drip -- in this instance, drip all over Nellie's little prick which was half-wedged into her hairy cunt where it had been twitching and thrusting as the two subs had received their strapping. It wasn't really a proper fucking, per se, but more like being frigged by a cocktail wiener. A nice appetizer, one might say, but hardly a main course.

"Alright, you two, brace yourself for your just desserts," Will told them. "Nellie, your Mommy has firmly instructed me to take your arse like a pirate does a cabin-boy's, so don't expect any mercy from me. I know you may be secretly enjoying this, but I'm not going to let you off easy."

Nellie groaned into Margaret's mouth and shuddered. Margaret gave his tongue an extra lick and suck and tried to smile encouragingly with her eyes. Nellie just looked panic-stricken, though Margaret could feel his little dick gain a little extra purchase in her twat. She knew from long experience that Nellie actually loved being terrorized. Constance knew it best of all, of course, which is why she kept him in a constant state of fear. She was "cruel to be kind" as the Nick Lowe song went.

Without further delay, Constance and Will plunged their rigid organs into their subs' tight anal passages. Muffled squeals emerged from Margaret's and Nellie's kiss-engorged mouths. A mix of slithery friction and suction was set in motion, as aggressive flesh-sticks plunged in and out of the helplessly bound subs' enflamed sphincters.

Will's gnarled member was rubbing up and down against Nellie's prostate, deep within his bowels, causing Nellie's diminutive prick to engorge itself within Margaret's sopping cunt, ballooning to an almost unheard of size.

Margaret's wrists were cuffed together hugging Nellie's neck. Will bent his head to kiss and suck on her fingers, caressing them with his tongue, heightening her arousal and reminding her of his loving control of her body. He was looking after her in the midst of her torment.

Connie's grotesque clitoris forced itself into Margaret's fundament and slithered in and out, while her cruel Mistress whispered huskily in Margaret's latex-encased ear. As in a trance, Margaret could barely make out the trash talk that Constance was assaulting her with.

"You're such a little slut, you really are. Everyone thinks you are so shy and proper, but I know better. You're nothing but a common whore hungry for her next fuck, the next spurt of cum all over her face, the next spray of piss soaking her hairy little cunt. You just wait, when I get done with you this weekend, your oh so gentle elderly Master will finally realize the utterly depraved slut he's taken on. We will see if he has buyer's remorse. Can he really service your needs like I can? Hmm? We shall see, you little fuck-pig."

This tirade so excited Constance that she began to scratch Margaret all over the areas of her flesh that had not already been painfully strapped. Spying Nellie's cuffed hands held against Margaret's shoulder blades before her, she began to bite poor Nellie's fingers, alternately licking them and chomping on them, relishing the sharp squeals this elicited from her servile husband. Connie was in a sadistic frenzy.